GB785468A - Preparation of fluid polyvalent metal phenates - Google Patents
Preparation of fluid polyvalent metal phenatesInfo
- Publication number
- GB785468A GB785468A GB201/55A GB20155A GB785468A GB 785468 A GB785468 A GB 785468A GB 201/55 A GB201/55 A GB 201/55A GB 20155 A GB20155 A GB 20155A GB 785468 A GB785468 A GB 785468A
- Authority
- GB
- United Kingdom
- Prior art keywords
- heated
- water
- phenol
- mixture
- methanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/235—Metal derivatives of a hydroxy group bound to a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
Oil-soluble polyvalent metal salts of phenolic compounds containing at least 10 carbon atoms for use as lubricating composition additives are produced, e.g. in mineral oil solution, by a process which comprises (a) preparing a solution of a polyvalent metal salt of the phenolic compound in a mixture containing a volatile organic solvent having a boiling point less than 170 DEG C., in which said salt is stable; (b) evaporating a major proportion of the volatile organic solvent from such solution at a temperature below the decomposition temperature of said polyvalent metal salt and (c) reacting the resulting material with from 0.1 to 2.5 moles. of water per mole. of polyvalent metal salt present. Phenolic compounds mentioned include alkylated phenols and naphthols and substitution products such chlorinated phenols and naphthols and phenol sulphides. Preferably, the phenolic compounds contain at least 10 aliphatic chain carbon atoms, preferably at least 20, in the form of alkyl or alkoxy radicals. Organic solvents mentioned include hydrocarbons, ethers, esters, alcohols and such ketones and aldehydes as are not reacted with phenolic compounds. Alcohols mentioned include methyl to iso-amyl and 2-methyl pentyl-4 alcohols. Basic metal salts may be prepared by forming the normal metal salts and after treatment with water and an excess of the appropriate metal alcoholate, further treating the product with water. Alternatively, the basic metal salt may be first prepared and treated with water. In examples: a mixture of magnesium methylate, methanol, octadecyl phenol and mineral oil is heated, concentrated and heated with water (1); in a similar process a polyisobutyl phenol containing an average of 32 carbon atoms per molecule is employed (2); dodecyl phenol is employed in a similar process (3); magnesium methylate in methanol is heated with the product of Example (2), the product is concentrated and treated with water (4); a mixture of sodium methylate, methanol octadecyl phenol and mineral oil is heated, zinc chloride in methanol is added and the mixture is concentrated and heated with water (5); polyisobutyl phenol is employed in a similar process (6); a mixture of sodium methylate, methanol, polyisobutyl-substituted phenol and zinc chloride is heated and concentrated, magnesium methylate in methanol is added and the mixture is heated, concentrated and again heated with water (7).ALSO:A method for producing a fluid, oil-soluble polyvalent metal salt of a phenolic compound, which phenolic compound contains a total of at least 10 carbon atoms, comprises the steps of (a) preparing a solution of a polyvalent metal salt of the phenolic compound in a mixture containing a volatile organic solvent having a boiling point less than 170 DEG C., in which said salt is stable; (b) evaporating a major proportion of the volatile organic solvent from such solution at a temperature below the decomposition temperature of said polyvalent metal salt; and (c) reacting with the resulting material from 0.1 to 2.5 mols. of water per mol. of polyvalent metal salt present. Phenolic compounds mentioned include alkylated phenols and naphthols and such substitution products as chlorinated phenols and naphthols and phenol sulphides. Preferably the phenolic compounds have in the molecule at least 10 aliphatic chain carbon atoms, preferably at least 20, e.g. in the form of alkyl or alkoxy radicals. Preferably such chains are derived from a polyisobutylene. Organic solvents mentioned include hydrocarbons, ethers, esters, alcohols and such ketones and aldehydes as are not reacted with phenolic compounds. Alcohols mentioned as suitable solvents include from methylto iso-amyl- and 2-methyl pentyl-4 alcohols. Basic metal salts may be prepared by forming the normal metal salts and after treatment with water and an excess of the appropriate metal alcoholate, further treating the product with water. Alternatively the basic metal salt may be first prepared and then treated with water. In examples: a mixture of magnesium methylate, methanol, octadecyl, phenol and mineral oil is heated under reflux, the product is concentrated under reduced pressure and the residue heated with water (1); in a similar process a polyisobutyl-substituted phenol containing an average of 32 carbon atoms per molecule is employed (2); dodecyl phenol is employed in a similar process (3); magnesium methylate in methanol is heated with the product of Example (2) and concentrated and treated with water (4); a mixture of sodium methylate, methanol, octadecyl phenol and minereal oil is heated, zinc chloride in methanol is added and the mixture is concentrated and the product is heated with water (5); a mixture of zinc chloride, sodium methylate, polyisobutyl phenol and mineral oil is heated, concentrated, and again heated with water (6); a mixture of sodium methylate, methanol, polyisobutyl-substituted phenol and zinc chloride is heated and concentrated, magnesium methylate in methanol is added and the mixture is heated, concentrated and again heated with water (7). Polyisobutyl phenol is prepared by heating phenol with a low molecular weight isobutylene polymer and a Friedel-Crafts catalyst, e.g. activated clay or aluminium chloride.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US785468XA | 1954-01-04 | 1954-01-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB785468A true GB785468A (en) | 1957-10-30 |
Family
ID=22144726
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB201/55A Expired GB785468A (en) | 1954-01-04 | 1955-01-04 | Preparation of fluid polyvalent metal phenates |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB785468A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2126602A (en) * | 1982-08-16 | 1984-03-28 | Maruzen Oil Co Ltd | Process for the production of basic alkaline earth metal phenates |
WO2017218657A3 (en) * | 2016-06-17 | 2018-01-18 | The Lubrizol Corporation | Polyisobutylene-substituted phenol, derivatives thereof, and lubricating compositions containing the polyisobutylene-substituted phenol and its derivatives |
US11572523B1 (en) | 2022-01-26 | 2023-02-07 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
US11976252B2 (en) | 2022-02-21 | 2024-05-07 | Afton Chemical Corporation | Polyalphaolefin phenols with high para-position selectivity |
-
1955
- 1955-01-04 GB GB201/55A patent/GB785468A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2126602A (en) * | 1982-08-16 | 1984-03-28 | Maruzen Oil Co Ltd | Process for the production of basic alkaline earth metal phenates |
WO2017218657A3 (en) * | 2016-06-17 | 2018-01-18 | The Lubrizol Corporation | Polyisobutylene-substituted phenol, derivatives thereof, and lubricating compositions containing the polyisobutylene-substituted phenol and its derivatives |
EP3472274B1 (en) * | 2016-06-17 | 2024-08-07 | The Lubrizol Corporation | Lubricating compositions containing a polyisobutylene-substituted phenol |
US11572523B1 (en) | 2022-01-26 | 2023-02-07 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
US11976250B2 (en) | 2022-01-26 | 2024-05-07 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
US11976252B2 (en) | 2022-02-21 | 2024-05-07 | Afton Chemical Corporation | Polyalphaolefin phenols with high para-position selectivity |
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